US6287603B1 - Cyclodextrin flavor delivery systems - Google Patents

Cyclodextrin flavor delivery systems Download PDF

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Publication number
US6287603B1
US6287603B1 US09/397,289 US39728999A US6287603B1 US 6287603 B1 US6287603 B1 US 6287603B1 US 39728999 A US39728999 A US 39728999A US 6287603 B1 US6287603 B1 US 6287603B1
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Prior art keywords
cyclodextrin
solution
flavor
active
percent
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Nikhil Prasad
David Straus
Glen Reichart
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Givaudan SA
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Nestec SA
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Priority to US09/397,289 priority Critical patent/US6287603B1/en
Priority to EP00110285A priority patent/EP1084625B1/en
Priority to AT00110285T priority patent/ATE320195T1/de
Priority to DE60026638T priority patent/DE60026638T2/de
Priority to SG200002928A priority patent/SG98403A1/en
Priority to MYPI20002400A priority patent/MY117225A/en
Priority to CA002310790A priority patent/CA2310790A1/en
Priority to JP2000223455A priority patent/JP2001089503A/ja
Priority to NZ506241A priority patent/NZ506241A/xx
Priority to KR1020000046135A priority patent/KR20010050028A/ko
Priority to NO20004567A priority patent/NO20004567L/no
Priority to PL00342510A priority patent/PL342510A1/xx
Priority to AU59415/00A priority patent/AU5941500A/en
Priority to IDP20000794D priority patent/ID27272A/id
Priority to ZA200004933A priority patent/ZA200004933B/xx
Priority to HU0003658A priority patent/HUP0003658A3/hu
Priority to BR0004231-5A priority patent/BR0004231A/pt
Publication of US6287603B1 publication Critical patent/US6287603B1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors

Definitions

  • the present invention relates to a method for preparing cyclodextrin complexes of actives, such as flavors, perfumes, pharmaceuticals, and the like wherein a higher percentage of active is complexed with the cyclodextrin compared to conventional methods of making cyclodextrin complexes.
  • actives such as flavors, perfumes, pharmaceuticals, and the like
  • the present invention also relates to the new cyclodextrin inclusion complexes, which can be prepared by the method.
  • cyclodextrins as a complexing agent for materials.
  • Cyclodextrins complexes are particularly desirable when the active is a flavoring material.
  • the flavoring material By complexing the flavoring material with a cyclodextrin the flavor material is protected from degradation as a result of reactions induced by heat, light, and/or reaction with oxygen or other compounds.
  • ⁇ -terpinene is a reactive terpene that is important in tangerine flavors.
  • ⁇ -terpinene is, however, easily oxidized to p-cymene which has an unpleasant kerosene note.
  • the ⁇ -terpinene with cyclodextrin the compound is protected from the adverse effects of oxygen and provides a flavor that is stable for a much longer period of time.
  • Complexing the flavoring material with a cyclodextrin also reduces loss of the flavor material by volatilization and/or sublimation.
  • diacetyl is a volatile compound that has a butter flavor. Due to its volatility the butter flavor is readily lost when food products containing diacetyl are heated. Complexing the diacetyl with cyclodextrin, however, leads to less butter flavor being lost when the food product is cooked in a microwave.
  • cyclodextrin complexes provide stable, standardized powders containing the active that are easy to use. Being a powder, the cyclodextrin complexes are easy to measure, handle, and store.
  • the increased stability of the flavor when complexed with cyclodextrin provides a flavor material that can be stored longer.
  • the longer storage times, easy handling, and simplicity of use all reduce costs and thus are of commercial importance in the food industry.
  • a further economic benefit of using cyclodextrin complexes is that less of the cyclodextrin complex is needed to flavor food compared to the natural spice or flavor.
  • cyclodextrin complexes Yet another advantage of cyclodextrin complexes is that the natural material content of some flavors can be reduced by complexing the flavor component(s) with cyclodextrin and thus the risk of allergic reactions is minimized and the risk of microbial contamination is reduced.
  • the content of the flavor in conventional cyclodextrin complexes typically ranges from about 5 to 15 percent, and more often from 7 to 10 percent.
  • Flavors typically consist of more than one component and while it is possible to complex all the components of the flavor composition with a cyclodextrin, generally only the more vulnerable components of the flavor composition are complexed.
  • Specific flavors and or flavor enhancers include, for example, those disclosed in U.S. Pat. Nos. 4,348,416 and 5,571,782.
  • flavors complexed with cyclodextrin include: U.S. Pat. No. 4,560,571 to Sato et al. that discloses an instant beverage in which soluble flavors and aromatic components present in roasted coffee beans, roasted beans, or roasted cereal are complexed with cyclodextrins; U.S. Pat. No. 4,529,608 to Szejtli et al. that discloses a process for the preparation of honey powder that preserves the aroma substance of the honey by complexing the aroma components with cyclodextrin; U.S. Pat. No. 3,061,444 to Rogers et al. that discloses complexing meat and vegetable aromas with cyclodextrin; U.S. Pat. No.
  • Complexing the flavor with cyclodextrin does not adversely effect the flavor, texture, or appearance of the food.
  • the food texture may actually be improved by complexing the flavor with a cyclodextrin.
  • soups and drinks prepared from mixes may be beneficially thickened when the flavor is complexed with a cyclodextrin.
  • Cyclodextrins are obtained by the action of the enzyme cycloglycosyltransferase on starches. In dilute aqueous solutions the enzyme connects the naturally occurring helixes in starch to form 3-dimensional polyglucose rings or crowns. Cyclodextrins are polyglucose rings created with 6, 7, or 8 glucose units and are referred to as ⁇ , ⁇ , or ⁇ cyclodextrins, respectively.
  • the external part of the crown like structure consists of primary and secondary hydroxyl groups and is hydrophilic.
  • the internal part of the crown consists mainly of carbon and hydrogen atoms and ether linkages and forms a hydrophobic cavity.
  • This macrocyclic structure with a hydrophilic exterior and hydrophobic interior allows the cyclodextrin molecule to form inclusion complexes with a wide variety of chemically different compounds referred to herein as actives.
  • the cyclodextrin behaves like a “host” that can accommodate, and release, the active or “guest” molecule.
  • cyclodextrin complexes A variety of methods are known to form cyclodextrin complexes. All these methods involve contacting the active with the cyclodextrin to form the complex. Typically, a warm aqueous solution of the cyclodextrin molecule is mixed with the active for sufficient time for the complex to form, followed by removal of the aqueous solvent. Alternatively, complexation can take place in an organic solvent or an aqueous solvent containing an organic cosolvent. Representative organic solvents include ethanol, isopropanol, acetone, and ethylacetate.
  • the active is combined with a small amount of solvent to form a paste and the cyclodextrin and paste are kneaded together to form the complex, followed by drying the resulting complex.
  • This method is commonly used when a high ratio of active to cyclodextrin is required.
  • the complex is filtered to remove the solvent and air-dried, dried in a vacuum oven, or freeze dried.
  • the complex may also be isolated by spray drying.
  • cyclodextrin complexes involve an equilibrium between the active complexed with the cyclodextrin, i.e., the complex, and the free active, i.e., the active not complexed with the cyclodextrin. Thus, a specific amount of free active is always present.
  • any free active is lost during the filtering and/or drying steps, and thus, the efficiency of the process is much less than 100%.
  • the efficiency of the process is measured as the percent yield for incorporation of the active, i.e., the amount of active recovered as a cyclodextrin complex divided by the starting amount of active.
  • the efficiency is generally only about 30 percent when cyclodextrin complexes are recovered by spray drying.
  • substantially more than 50 percent of the active can be lost during the drying step. This loss of active increases the cost of the final product and is especially problematic for expensive actives.
  • the present invention relates to new higher loading cyclodextrin inclusion complexes containing one or more actives and to a process for preparing such complexes.
  • the process comprises the steps of dissolving cyclodextrin in a solvent in a reaction vessel to form a first solution, adding the one or more actives to the first solution with stirring to form a second solution of the one or more actives and cyclodextrin, stirring the second solution for a sufficient amount of time and at a sufficient temperature to form inclusion complexes between the cyclodextrin and the one or more actives, adding a solids content increasing agent to the second solution to increase the solids content of the second solution and form a third solution, and drying the third solution to form the cyclodextrin inclusion complex as a dry powder.
  • the concentration of cyclodextrin in the second solution may be between about 5 and 40 percent and the ratio of active to cyclodextrin may be between about 0.001:1 and 100:1.
  • the temperature of the second solution may be between about 4° C. and 75° C.
  • reaction vessel is sealed and the active is added without opening the reaction vessel.
  • the reaction vessel may also be pressurized.
  • the reaction vessel may be pressurized to a value of above atmospheric to about 1000 psi.
  • the second solution is stirred at a first temperature for a first length of time, the temperature of the second solution is then progressively lowered to one or more subsequent temperatures, and the lowered temperature of the second solution is maintained while the second solution is stirred.
  • the solids content increasing agent is preferably at least one of gum acacia, maltodextrin, or modified starch, and may be added to increase the solids content of the second solution to about 30 to 55 percent by weight of the solution.
  • the solids content of the second solution may conveniently be increased by adding gum acacia in an amount of about 5 to 20 percent by weight of the solution and the remaining solids content increased by adding about 40 to 60 percent by weight of the solution of a maltodextrin having a dextrose equivalent of between about 5 and 10.
  • the active may be one or more pharmaceuticals, perfumes, or flavor components.
  • the flavor component can be dimethyl sulfide, methyl mercaptan, acetaldehyde, 2-methyl-3-furanthiol, diacetyl, flavors produced by pyrolysis, or mixtures thereof.
  • the invention also relates to cyclodextrin inclusion complexes prepared according to the process of the invention.
  • the cyclodextrin inclusion complex may contain between about 1 and 20 percent by weight of the complex, and conveniently is above 15 percent by weight of complex.
  • the active in the cyclodextrin inclusion complex may be one or more flavors, perfumes, or pharmaceuticals.
  • FIG. 1 is a schematic drawing of a reaction vessel for preparing cyclodextrin complexes according to the present invention
  • FIG. 2 is a graph comparing the efficiency of the process of the present invention for complexing tomato flavor with cyclodextrins with the efficiency of several other methods of complexing or encapsulating tomato flavor;
  • FIG. 3 is a graph representing the results of a technical screening panel that compared the quality of tomato, chicken, and shrimp flavors complexed with cyclodextrin according to the process of the present invention with those flavors encapsulated by conventional spray drying;
  • FIG. 4 is a graph representing the results of a technical screening panel that compared the quality of tomato flavor complexed with cyclodextrin according to the process of the present invention with tomato flavors encapsulated by conventional spray drying as a function of time;
  • FIG. 5 is a graph representing the results of a technical screening panel that compared the quality of chicken flavor complexed with cyclodextrin according to the process of the present invention with chicken flavor encapsulated by conventional spray drying as a function of time;
  • FIG. 6 is a graph representing the results of a technical screening panel that compared the quality of shrimp flavor complexed with cyclodextrin according to the process of the present invention with shrimp flavor encapsulated by conventional spray drying as a function of time;
  • FIG. 7 is a graph representing a comparison of the stability of tomato, chicken, and shrimp flavors complexed with cyclodextrin according to the process of the present invention with those flavors encapsulated by conventional spray drying after storage at 25° C. or 40° C. and relative humidity of 53 percent.
  • the present invention is directed at a process for complexing actives with cyclodextrins.
  • the process of the present invention increases the efficiency of the complexation so that a higher percentage of the active is recovered as a cyclodextrin inclusion complex.
  • the invention is also directed at the product produced by the complexation process.
  • any active can be complexed with cyclodextrin according to the invention, including but not limited to flavors, perfumes, and pharmaceuticals.
  • the process is particularly suitable in connection with actives that are flavors and will be described predominately in that context. It is to be appreciated, however, that this is done for simplicity of description and the process is not limited to this application.
  • the process of the invention involves adding a cyclodextrin to a solvent in a reaction vessel, adding an active to the cyclodextrin solution with stirring and without opening the sealed reaction vessel, and allowing the mixture to stir for an appropriate amount of time and at a sufficient temperature to form an inclusion complex between the cyclodextrin and the active.
  • a solids content increasing agent is then added to the solution to increase the solids content of the solution and the solution is spray dried to recover the cyclodextrin-active inclusion complex as a dry powder.
  • the reaction vessel may be sealed or unsealed. Preferably the reaction vessel is sealed to avoid the loss of any volatile components.
  • any solids content increasing agent may be used, including but not limited to, maltodextrins and low dextrose equivalent corn syrup solids (5, 10, 15 and 20 DE); enzyme modified starches, oxidized starches (for example starch oxidized with hypochlorite or periodate); amino acid substituted corn starch derivatives (for example, periodate-oxidized corn starch, amylase-dextrinized corn starch, and corn starch covalently attached to phenyalanine glycoamine); oligosaccharides from alpha-amylase modified starches of wheat, maize, rice, amylomaize, corn, waxy corn, cassava, and Potato; octenylsuccinate treated starch; hydrocolloids (for example, gum acacia, xanthan, guar, locust bean, tragacanth, and carrageenan); and proteins (for example, milk powder, whey, and soy).
  • the solids content increasing agent is gum acacia,
  • any cyclodextrin that forms a complex with the active can be used.
  • the cyclodextrin is an ⁇ - or ⁇ - or ⁇ -cyclodextrin.
  • Any solvent can be used that dissolves the cyclodextrin, however, the preferred solvent is water.
  • a co-solvent such as ethanol or isopropyl alcohol may be added to the water. Typically, when a cosolvent is used it is added to water in an amount of about 1 or 2 percent.
  • the concentration of cyclodextrin in the solution is preferably between about 5 percent to 40 percent by weight and preferably between about 15 percent and 20 percent by weight. It is, however, not necessary that all of the cyclodextrin be dissolved when it is added to the solvent. It is satisfactory for an equilibrium to be established between dissolved and undissolved cyclodextrin. In general, the concentration of cyclodextrin in solution increases with increasing temperature.
  • the mixture is typically stirred at a rate of between about 300 rpm and 1500 rpm, preferably 300 to 500 rpm.
  • the higher the agitation rate the faster the rate of formation of the cyclodextrin-active inclusion complex.
  • the stirring rate cannot be so high as to create sufficient shear to breakdown the cyclodextrin molecules.
  • the stirring rate should be as high as possible without damaging the cyclodextrin molecules.
  • the active is introduced into the stirred Solution of cyclodextrin.
  • the active is introduced to a sealed reaction vessel without opening the reaction vessel.
  • the active is pumped into the reactor in pure form or as a solution and the lines of the flavor delivery system are rinsed with solvent.
  • the active is added as a solution it is preferably added at the highest concentration possible.
  • the concentration of active in the solution is greater than 50 percent by weight and more preferably greater than 80 percent by weight.
  • the active is a flavor the preferred solvents for the flavor are oil-based , fixed oil, triacetin, or water. The concentration of active present in the resulting solution is determined by the flavor load that is desired in the final product.
  • the necessary concentration of active in the final solution can readily be determined by one of ordinary skill in the art with routine experimentation.
  • the flavor load of the active in the final product is between 1 and 20 percent, preferably between 2 and 10 percent.
  • the mole ratio of active to cyclodextrin in the resulting solution is between about 0.001:1 and about 100:1, preferably, between about 0.01:1 and 10:1, and more preferably between about 0.2:1 and 1:5.
  • the temperature of the solution is generally between about 4° C. and 75°C, preferably between about 10° C. and 40° C., and more preferably between about 12° C. and 30° C.
  • the time for forming the complex is typically between 15 minutes and about 24 hours, preferably between 1 hour and 10 hours. In general the higher the temperature the shorter the reaction time. Without wishing to be bound by theory it is believed that the shorter reaction times at higher temperatures is due to more of the cyclodextrin being dissolved in the solvent at higher temperatures. Typical reaction times are 4 hours at 25° C.
  • complexation can be initiated with stirring at a high temperature followed by progressively lowering the temperatures.
  • Applicants have, unexpectedly found that formation of the inclusion complex is more efficient when the temperature of the solution is varied.
  • Formation of the inclusion complex can be more efficient when the complexation is initiated with stirring at a high temperature followed by progressively lower temperatures.
  • the mixture may be held under constant agitation for 1 hour at 75° C. followed by 3 hours at 25° C. and 20 hours at 11° C.
  • the efficiency of inclusion complex formation may be increased if the reaction vessel is maintained under a positive pressure.
  • the formation of the inclusion complex takes place under positive pressure.
  • the pressure can be increased to any value, however, the pressure is typically above atmospheric and up to as high as about 1000 psi (68 bar), more preferably up to about 100 psi (6.8 bar). Increasing the pressure during complexation is particularly beneficial when the active is volatile.
  • the total solids content of the resulting slurry is increased to about 30 to 55 percent by weight, preferably 35 to 41 percent by weight by adding a solids content increasing agent, i.e., gum acacia, maltodextrin, modified dextrins, or mixtures thereof.
  • a solids content increasing agent i.e., gum acacia, maltodextrin, modified dextrins, or mixtures thereof.
  • gum acacia is added in an amount between about 5 to 20 percent by weight, preferably about 7 to 15 percent by weight, and more preferably about 8 to 10 percent by weight and the remaining solids content is made up with maltodextrin having a dextrose equivalent (DE) of between about 5 and 10.
  • DE dextrose equivalent
  • the maltodextrin is added in an amount of between about 30-80% by weight, preferably 40-60% by weight.
  • the resulting mixture is then dried preferably by using conventional spray drying techniques that are well known to those of ordinary skill in the art
  • the dried cyclodextrin complexes produced according to the process of the present invention have a higher percent of active complexed with the cyclodextrin than if the cyclodextrin complex was prepared by traditional methods such as filtering the cyclodextrin inclusion complex and freeze drying or vacuum drying the filtrate, or spray drying a solution of the cyclodextrin inclusion complex without the addition of the solids content increasing agent of gum acacia, maltodextrin, modified dextrins, or mixtures thereof.
  • the process of the present invention complexes a significantly higher percentage of active compared to traditional spray drying process that do not involve forming cyclodextrin inclusion complexes but merely adsorbs the active on the surface of or encapsulates the active in the pores of a solid particle such as gum acacia, maltodextrin, or modified dextrins.
  • the increased efficiency is particularly evident when the active is volatile.
  • typical spray drying has an efficiency of only about 8 percent and spray drying a cyclodextrin inclusion complex without gum acacia, maltodextrin, modified dextrins, or mixtures thereof has an efficiency of about 33 percent.
  • the efficiency of the process is better than 75 percent.
  • the process of the present invention recovers more of the active in the form of an inclusion complex compared to other methods of encapsulating actives and results in less of the active being loot.
  • the increased efficiency is the result of a second coating of gum acacia, maltodextrin, modified dextrins, or mixtures thereof forming on the cyclodextrin-active inclusion complex.
  • the increased efficiency may also be partly due to free active, i.e., active not complexed with cyclodextrin, being adsorbed onto the surface of or encapsulated in the pores of the gum acacia, maltodextrin, modified dextrins, or mixtures thereof.
  • the process of the present invention produce a cyclodextrin inclusion complex that has a higher percent of active complexed therein compared to other processes of preparing cyclodextrin inclusion complexes.
  • the increased amount of active in the inclusion complex less of the final material is needed to have a given effect, such as producing an aroma in a perfume or a flavor in a food. This increased efficiency means that the cost of producing cyclodextrin inclusion complex is significantly reduced such that the process becomes cost effective and commercially practical.
  • the process of the present invention is particularly economical for expensive actives or actives that are volatile. Moreover, the process of the present invention can be used to form an inclusion complex with only a specific component of a flavor or aroma composition, for example, and to then dry blending the resulting complex back with the other components of the composition.
  • the specific component is a volatile component of the flavor or aroma composition or a component that is subject to degradation on exposure to air, light, oxygen, or other compounds.
  • the process of the invention is particularly useful for forming cyclodextrin complexes with dimethyl sulfide, methyl mercaptan, acetaldehyde, 2-methyl-3-furanthiol, and diacetyl.
  • the process of the present invention is particularly useful to form cyclodextrin complexes with pyrolyzed flavors.
  • Pyrolyzed flavors are free fatty acids that are pyrolyzed at a high temperature and provide a grilled or fatty note to foods.
  • a problem with pyrolyzed flavors is that they are unstable in the presence of hydrolyzed plant proteins, however, if the pyrolyzed flavors are complexed in a cyclodextrin inclusion complex their stability in the presence of hydrolyzed plant proteins is improved significantly.
  • flavor component is meant any compound or mixture of compounds that contribute to the overall flavor perception.
  • Flavor components include, but are not limited to, those listed in the 21 FEMA GRAS list, the Codex Alimentarius list, or any other reliably published list, spices, oleoresins, flavor enhancers, and the like
  • the invention is also directed at a composition prepared according to the method described above.
  • the composition comprises one or more actives in a powdered form wherein at least a portion of the active is complexed with cyclodextrin and the cyclodextrin is coated with gum acacia, maltodextrin, modified starch, or mixtures thereof.
  • the active may be a flavor, perfume, pharmaceutical, and the like.
  • the active typically comprises between about 1 and 20 percent by weight of the complex, and often greater than 15% of the complex.
  • the cyclodextrin complexes of the present invention show the same flavor release and stability as other encapsulated flavors.
  • Complexes were formed in a 4-liter reactor vessel that had an agitator and temperature control.
  • the reactor vessel is depicted in FIG. 1 .
  • the agitation speed was set at 1500 rpm.
  • 1 liter of a 15% solution of ⁇ -cyclodextrin (CavitronTM, commercially available from Cerestar of Hammond, Ind.) was heated to 75° C. and transferred to the reactor vessel.
  • the container holding the flavor was rinsed with 100 ml of water and the water pumped into the reaction vessel.
  • the sample was continually stirred at 1500 rpm for 1 hour at 75° C.
  • the amount of flavor component in the inclusion complex was determined using headspace gas chromatographic (GC) analysis with a PE8500 gas chromatograph (commercially available from Perkin Elmer of Norwalk, Conn.) equipped with a flame ionization detector. The amount of flavor component was determined based on the peak response of key marker molecules for each flavor. External standards were used to establish retention times for marker molecules.
  • GC headspace gas chromatographic
  • Samples for analysis were prepared by dissolving 100 mg of the inclusion complex or 25 mg of the inclusion complex formed from tomato flavor in 1 mL of water in a 20 mL air tight vial.
  • the samples were placed in a PE101 Auto-sampler (commercially available from Perkin Elmer of Norwalk, Conn.) and heated to 80° C. 2 ⁇ L of static headspace samples was injected onto a 75 m ⁇ 0.53 mm ⁇ 3-micron J&W DB624 column (commercially available from J&W Scientific Co. of Folsom, Calif.).
  • the following chromatographic conditions were used: initial temperature of 70° C. with a hold time of 3 minutes followed by a linear temperature gradient from 70° C.
  • Tomato flavor was complexed with ⁇ -cyclodextrin according to the process described above and the amount of the marker molecule dimethyl sulfide (DMS) in the inclusion complex was determined by headspace GC analysis.
  • tomato flavor was also complexed with ⁇ -cyclodextrin according to the process described above except that gum acacia and maltodextrin were not added to increase the solids content before spray drying.
  • tomato flavor was also encapsulated by spray drying with gum acacia and maltodextrin alone. In this experiment the process described above was followed except that maltodextrin was substituted for cyclodextrin during complexation and the resulting slurry was spray dried.
  • the efficiency of the process according to the present invention was 75 percent.
  • the efficiency of spray drying the cyclodextrin inclusion complex without gum acacia and maltodextrin was only 33 percent and the efficiency of encapsulation by spray drying with gum acacia and maltodextrin alone was only 8 percent.
  • FIG. 2 provides this data graphically. The results show that the process of the present invention is much more efficient than conventional methods of encapsulating flavor components.
  • Example 2 Comparison of Spray Drying ⁇ -cyclodextrin Complexes with Gum Acacia and Maltodextrin with Other Methods of Drying ⁇ -cyclodextrin Inclusion Complexes.
  • Flavor (arbitrary (arbitrary (arbitrary Molecule units) units) units) Dimethyl 881,024 7,635,105 8,852,907 sulfide Cis-3-hexenol 7,910 31,858 29,941 2-isobutyl 7,734 14,076 16,912 thiazole Phenylethyl 324 204 368 alcohol ⁇ -damescenone 61,107 128,022 164,493
  • Tomato flavor was complexed with ⁇ -cyclodextrin as described in above.
  • tomato flavor was complexed with ⁇ -cyclodextrin according to the procedure described above except that the temperature during the 24-hour complexation period was maintained at 25° C. Results are provided in Table 2.
  • Flavor hrs. (arbitrary (arbitrary Percent Molecule units) units) Increase Dimethyl 3,342,209 7,635,105 56 sulfide Cis-3-hexenol 11,623 31,858 64 2-isobutyl 7,978 14,076 43 thiazole Phenylethyl 150 204 26 alcohol ⁇ -damescenone 115,533 128,022 10
  • the effect of pressure on the efficiency of complexation was evaluated by completing the components of tomato flavor with ⁇ -cyclodextrin according to the process described above.
  • the complexation was conducted at atmospheric pressure, 100 psi, and 1000 psi.
  • Table 3 shows that increasing the pressure improves the efficiency of the process, as measured by peak area from GC headspace, for dimethyl sulfide and isobutyl thiazole.
  • Table 3 also shows that for ⁇ -damescenone and cis-3-hexenol increasing the pressure initially led to an increase in the amount of flavor completed with the cyclodextrin but the effect leveled off.
  • Flavor Compounds Entrapped in ⁇ -cyclodextrin with Tomato Flavor Amount Entrapped at Amount Atmospheric Entrapped Amount
  • Entrapped Pressure at a 100 psi at 1000 psi (arbitrary (arbitrary (arbitrary units) units) units) Dimethyl sulfide 6,903,774 8,914,755 9,577,128 Cis-3-hexenol 25,638 37,636 36,863 2-isobutyl 13,622 15,065 16,157 thiazole Phenylethyl 553 440 199 alcohol ⁇ -damescenone 133,786 142,919 138,858
  • Example 5 Comparison of Flavor Ouality for Flavors Complexed with ⁇ -Cyclodextrins According to the Process of the Present Invention with Flavors Spray Dried with Gum Acacia and Maltodextrin.
  • Samples of tomato, shrimp, and chicken flavor were complexed with ⁇ -cyclodextrins as described above.
  • samples were also encapsulated by conventional spray drying of these flavors with gum acacia and maltodextrin. Conventional spray drying of these flavors was performed as described in Example 1 for tomato flavor.
  • the encapsulated flavors were added to a dehydrated TRIOTM system (commercially available from Nestle Food Services of Solon, Ohio) to produce a base flavor system.
  • the TRIOTM system is a neutral flavored powder for preparing sauces.
  • the base flavor systems were prepared by adding the chicken and shrimp complexes to the TRIOTM system at a 10 percent level and by adding the tomato complex at a 5 percent level.
  • the base flavor systems were then rehydrated with hot water (100° C.) and tasted by a technical screening panel.
  • Bases containing the chicken and shrimp complexeo were tasted as a 2 percent solution in hot water and bases containing the tomato flavor were tasted as a 4 percent solution in hot water.
  • the technical screening panel had a minimum of eight members at each tasting session.
  • a 10-point intensity scale was used to judge the intensity of flavors with 0 indicating a dislike of the flavor and 10 indicating an extreme liking of the flavor.
  • Samples were first evaluated by the panel and an arbitrary unit was chosen on the 10 point scale to rate the model system which was fresh spray dried powder.
  • An arbitrary unit was also chosen to rate the spray-dried powder and the flavor complexed with ⁇ -cyclodextrin, which compared these flavors relative to the model system. These values were designated as time zero values for each flavor. Further evaluations were based on this scale.
  • the screening panel was provided with the model system and the unit value that was assigned to the model system, samples were than rated on the 10-point scale relative to the model system.
  • FIG. 3 shows the result of the technical screening panel for tomato, chicken, and shrimp flavors. The results show that upon rehydration the flavor complexed with ⁇ -cyclodextrin according to the present invention performed equal to or better than their spray dried counterpart.
  • Samples of tomato, beef, and chicken flavor were complexed with ⁇ -cyclodextrins as described above.
  • samples were also encapsulated by conventional spray drying of these flavors with gum acacia and maltodextrin following the procedure described in Example 1 for tomato flavor.
  • Samples were then stored at of temperature of 25° C. or 40° C. in a desiccator containing a saturated solution of magnesium nitrate to control the relative humidity at a level of 53%.
  • the 40° C. samples were evaluated by headspace chromatography at 1 week intervals for 8 weeks and the 25° C. samples were evaluated at the 3 and 5 month intervals. Samples were also evaluated by the technical panel at time zero and after 8 weeks for samples stored at 40° C. and after 3 months for samples stored at 25° C.
  • FIG. 7 shows the results of the technical panel for each flavor. Again it was observed that the ⁇ -cyclodextrin flavor complexes had a higher flavor intensity compared to their spray-dried counterparts. This, higher intensity for the ⁇ -cyclodextrin flavor complexes is again attributed to the fact that there was more flavor incorporated into ⁇ -cyclodextrin flavor complex at the start.

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US09/397,289 US6287603B1 (en) 1999-09-16 1999-09-16 Cyclodextrin flavor delivery systems
EP00110285A EP1084625B1 (en) 1999-09-16 2000-05-23 Flavor delivery system
AT00110285T ATE320195T1 (de) 1999-09-16 2000-05-23 Aromafreigabesystem
DE60026638T DE60026638T2 (de) 1999-09-16 2000-05-23 Aromafreigabesystem
SG200002928A SG98403A1 (en) 1999-09-16 2000-05-30 Cyclodextrin flavor delivery systems
MYPI20002400A MY117225A (en) 1999-09-16 2000-05-30 Cyclodextrin flavor delivery systems
CA002310790A CA2310790A1 (en) 1999-09-16 2000-06-06 Cyclodextrin flavor delivery systems
JP2000223455A JP2001089503A (ja) 1999-09-16 2000-07-25 シクロデキストリン包接複合体およびその製造方法
NZ506241A NZ506241A (en) 1999-09-16 2000-08-09 Solid cyclodextrin flavor delivery systems
KR1020000046135A KR20010050028A (ko) 1999-09-16 2000-08-09 시클로덱스트린 향미 전달 시스템
NO20004567A NO20004567L (no) 1999-09-16 2000-09-13 Syklodekstrinholde smaksstoff-leverende systemer
PL00342510A PL342510A1 (en) 1999-09-16 2000-09-13 Aroma providing cyclodextrin systems
AU59415/00A AU5941500A (en) 1999-09-16 2000-09-13 Cyclodextrin flavor delivery systems
IDP20000794D ID27272A (id) 1999-09-16 2000-09-14 Sistem pemberian rasa cyclodextrin
ZA200004933A ZA200004933B (en) 1999-09-16 2000-09-15 Cyclodextrin flavor delivery systems.
HU0003658A HUP0003658A3 (en) 1999-09-16 2000-09-15 Cyclodextrin flavor delivery systems
BR0004231-5A BR0004231A (pt) 1999-09-16 2000-09-15 Sistemas de liberação de aroma de ciclodextrina

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Cited By (48)

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Publication number Priority date Publication date Assignee Title
US6638557B2 (en) * 2001-08-14 2003-10-28 Cerestar Holding B.V. Dry, edible oil and starch composition
US20040057910A1 (en) * 2002-09-24 2004-03-25 The Procter & Gamblecompany Oral products having an aesthetic layer
US20040109920A1 (en) * 2002-12-04 2004-06-10 Bioactives Llc Coated carotenoid cyclodextrin complexes
US20040180125A1 (en) * 2003-03-11 2004-09-16 Plank David W. Cyclodextrin-containing compositions and methods
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US20040192576A1 (en) * 2003-03-24 2004-09-30 Wacker Biochem Corp. Cyclodextrin laundry detergent additive complexes and compositions containing same
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US20060088648A1 (en) * 2004-10-15 2006-04-27 Teoh Heidi M Microwave popcorn with thaumatin and method of preparation
US20060134132A1 (en) * 2004-12-20 2006-06-22 Watkins Jackie M Protective barriers for micronutrients, phytochemicals, and nutraceuticals
WO2008073935A1 (en) * 2006-12-13 2008-06-19 Dow Global Technologies Inc. Method and composition for removal of mercaptans from gas streams
US20080283693A1 (en) * 2007-05-15 2008-11-20 Evans Michael J F Propulsion apparatus and system
US20090022856A1 (en) * 2007-07-16 2009-01-22 Philip Morris Usa Inc. Oral pouch products with immobilized flavorant particles
US20090029020A1 (en) * 2005-06-13 2009-01-29 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20090185985A1 (en) * 2006-06-13 2009-07-23 Cargill, Incorporated Large-particle cyclodextrin inclusion complexes and methods of preparing same
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US20100324512A1 (en) * 2009-06-18 2010-12-23 Mariangela Caputi Absorbent articles comprising an odour control system
US20110028431A1 (en) * 2009-07-31 2011-02-03 Zerbe Horst G Oral mucoadhesive dosage form
US20110281940A1 (en) * 2007-09-05 2011-11-17 Macrocare Tech., Ltd. Method of preparation an inclusion-complex comprising hydrophobic physiological activation material including with cyclodextrin and its use
DE102010023790A1 (de) 2010-06-15 2011-12-15 Heinrich-Heine-Universität Düsseldorf Waschaktive Zusammensetzung
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US8424541B2 (en) 2007-07-16 2013-04-23 Philip Morris Usa Inc. Tobacco-free oral flavor delivery pouch product
US8685478B2 (en) 2005-11-21 2014-04-01 Philip Morris Usa Inc. Flavor pouch
US8747562B2 (en) 2009-10-09 2014-06-10 Philip Morris Usa Inc. Tobacco-free pouched product containing flavor beads providing immediate and long lasting flavor release
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Citations (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3061444A (en) 1960-10-07 1962-10-30 Gen Foods Corp Inclusion compounds incorporating edible juice constituents
US3140184A (en) 1959-10-29 1964-07-07 Gen Foods Corp Edible materials containing water soluble dextrin forming complexes
US3816393A (en) 1970-06-10 1974-06-11 Ono Pharmaceutical Co Clathrate compounds of prostaglandins or their analogues with cyclo-dextrin
US3846551A (en) 1972-11-20 1974-11-05 Teijin Ltd Insecticidal and acaricidal composition and process for controlling pests
US4001438A (en) 1974-10-15 1977-01-04 International Flavors & Fragrances Inc Flavor composition for use in orally utilizable compositions
US4024223A (en) 1972-11-11 1977-05-17 Teijin Limited Stripe composition and method of reducing smell associated therewith
US4054736A (en) 1970-06-10 1977-10-18 Ono Pharmaceutical Co., Ltd. Clathrate compounds of prostaglandins or their analogues with cyclodextrin
US4073931A (en) 1974-03-27 1978-02-14 Teijin Limited Nitroglycerine inclusion compounds with cyclodextrin and composition containing same
US4228160A (en) 1978-01-27 1980-10-14 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Inclusion complex of cyclodextrin and indomethacin and a process for the preparation thereof, method of use and pharmaceutical composition
US4247535A (en) 1979-11-05 1981-01-27 American Cyanamid Company Modified cyclodextrin sulfate salts as complement inhibitors
US4265779A (en) 1978-09-09 1981-05-05 The Procter & Gamble Company Suds suppressing compositions and detergents containing them
US4268501A (en) 1978-12-29 1981-05-19 Yamanouchi Pharmaceutical Co., Ltd. Suppositories containing a compound having bronchodilator activity
US4296137A (en) 1980-08-07 1981-10-20 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate
US4296138A (en) 1980-08-07 1981-10-20 International Flavors & Fragrances Inc. Flavoring with 1-n-butoxy-1-ethanol acetate
GB2074838A (en) * 1980-02-18 1981-11-11 Chinoin Gyogyszer Es Vegyeszet Tea aromatizing compositions and tea aromatized therewith
US4348416A (en) 1980-08-07 1982-09-07 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate - acetaldehyde mixtures
US4365061A (en) 1980-10-17 1982-12-21 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Inclusion complexes of cyclodextrins and strong inorganic oxy-acids and process for their preparation
US4371673A (en) 1980-07-21 1983-02-01 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Water soluble forms of retinoids
US4380626A (en) 1979-12-28 1983-04-19 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Hormonal plant growth regulator
US4438106A (en) 1981-07-16 1984-03-20 Kureha Kagaku Kabushiki Kaisha Inclusion compound of eicosapentaenoic acid or docosahexaenoic acid with cyclodextrin
US4474822A (en) 1980-08-09 1984-10-02 Sata Shokuhin Kogyo Kabushiki Kaisha Process for the preparation of instant tea
US4529608A (en) 1982-11-08 1985-07-16 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt Honey powder preserving its natural aroma components
US4547365A (en) 1982-11-08 1985-10-15 Shiseido Company Ltd. Waving lotion for cold waving
US4596795A (en) 1984-04-25 1986-06-24 The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives
US4616008A (en) 1984-05-02 1986-10-07 Takeda Chemical Industries, Ltd. Antibacterial solid composition for oral administration
US4632832A (en) 1984-08-15 1986-12-30 Morinaga Milk Industry Co., Ltd. Instant creaming powder
US4636343A (en) 1984-09-10 1987-01-13 Ichiro Shibanai Process for the preparation of insect repelling/killing film
US4663316A (en) 1985-06-28 1987-05-05 Warner-Lambert Company Antibiotic clathrates and pharmaceutical compositions thereof
US4675395A (en) 1984-03-14 1987-06-23 Seiwa Technological Laboratories Limited Cyclodextrin inclusion compound and process for its preparation
US4728510A (en) 1985-06-13 1988-03-01 Japan Liquid Crystal Co., Ltd. Bath preparations and method for producing the same
US4732759A (en) 1985-06-13 1988-03-22 Japan Liquid Crystal Co., Ltd. Bath preparations and method for producing the same
US4751095A (en) 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US5571782A (en) 1990-03-06 1996-11-05 The Procter & Gamble Company Solid consumer product compositions containing small particle cyclodextrin complexes

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU174699B (hu) * 1977-07-01 1980-03-28 Chinoin Gyogyszer Es Vegyeszet Sposob poluchenija natural'nykh i sinteticheskikh ciklodektrinnykh okkluzionnykh kompleksov prjaznostej, aromatov i vkusnykh vehhestv
JPS62120344A (ja) * 1985-11-20 1987-06-01 Nippon Redarii Kk ４−ビフエニリル酢酸エステル−シクロデキストリン包接化合物
JPS6463552A (en) * 1987-09-04 1989-03-09 Lederle Japan Ltd 4-biphenylylacetic acid ester-cyclodextrin inclusion compound
CA1321192C (en) * 1988-04-20 1993-08-10 Abdul Majid Inclusion complexes of cyclodextrins by agglomeration
GB8813682D0 (en) * 1988-06-09 1988-07-13 Reckitt & Colmann Prod Ltd Pharmaceutical compositions
US5206025A (en) * 1989-05-24 1993-04-27 Rhone-Poulenc Sante Porous pharmaceutical form and its preparation
FR2647343B1 (fr) * 1989-05-24 1994-05-06 Rhone Poulenc Sante Nouvelle forme pharmaceutique poreuse et sa preparation
FR2665613B1 (fr) * 1990-08-13 1993-02-12 Orsan Aromes de vins et d'alcools forts en poudre.
CA2119578A1 (en) * 1991-09-21 1993-04-01 Shusei Ito Complex of compound having chalcone skeleton
HUT63704A (en) * 1991-11-20 1993-09-28 Forte Fotokemiai Ipar Method for accelerating development of photo-materials
JPH06248194A (ja) * 1993-02-25 1994-09-06 Ensuiko Sugar Refining Co Ltd ケルセチン含有着色料
US5780089A (en) * 1996-05-03 1998-07-14 Nestec S.A. Flavor composition
JPH10167958A (ja) * 1996-12-09 1998-06-23 Sankyo Co Ltd ロキソプロフェンナトリウム類を含有する口腔内速溶性製剤及びその製造方法
JPH10330403A (ja) * 1997-06-04 1998-12-15 Yamasan:Kk 新規包接体、その用途及び樹脂組成物

Patent Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3140184A (en) 1959-10-29 1964-07-07 Gen Foods Corp Edible materials containing water soluble dextrin forming complexes
US3061444A (en) 1960-10-07 1962-10-30 Gen Foods Corp Inclusion compounds incorporating edible juice constituents
US3816393A (en) 1970-06-10 1974-06-11 Ono Pharmaceutical Co Clathrate compounds of prostaglandins or their analogues with cyclo-dextrin
US4054736A (en) 1970-06-10 1977-10-18 Ono Pharmaceutical Co., Ltd. Clathrate compounds of prostaglandins or their analogues with cyclodextrin
US4024223A (en) 1972-11-11 1977-05-17 Teijin Limited Stripe composition and method of reducing smell associated therewith
US3846551A (en) 1972-11-20 1974-11-05 Teijin Ltd Insecticidal and acaricidal composition and process for controlling pests
US4073931A (en) 1974-03-27 1978-02-14 Teijin Limited Nitroglycerine inclusion compounds with cyclodextrin and composition containing same
US4001438A (en) 1974-10-15 1977-01-04 International Flavors & Fragrances Inc Flavor composition for use in orally utilizable compositions
US4228160A (en) 1978-01-27 1980-10-14 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Inclusion complex of cyclodextrin and indomethacin and a process for the preparation thereof, method of use and pharmaceutical composition
US4265779A (en) 1978-09-09 1981-05-05 The Procter & Gamble Company Suds suppressing compositions and detergents containing them
US4268501A (en) 1978-12-29 1981-05-19 Yamanouchi Pharmaceutical Co., Ltd. Suppositories containing a compound having bronchodilator activity
US4247535A (en) 1979-11-05 1981-01-27 American Cyanamid Company Modified cyclodextrin sulfate salts as complement inhibitors
US4380626A (en) 1979-12-28 1983-04-19 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Hormonal plant growth regulator
GB2074838A (en) * 1980-02-18 1981-11-11 Chinoin Gyogyszer Es Vegyeszet Tea aromatizing compositions and tea aromatized therewith
US4371673A (en) 1980-07-21 1983-02-01 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Water soluble forms of retinoids
US4296137A (en) 1980-08-07 1981-10-20 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate
US4296138A (en) 1980-08-07 1981-10-20 International Flavors & Fragrances Inc. Flavoring with 1-n-butoxy-1-ethanol acetate
US4348416A (en) 1980-08-07 1982-09-07 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate - acetaldehyde mixtures
US4474822A (en) 1980-08-09 1984-10-02 Sata Shokuhin Kogyo Kabushiki Kaisha Process for the preparation of instant tea
US4560571A (en) 1980-08-09 1985-12-24 Sato Shokuhin Kogyo Kabushiki Kaisha Process for the preparation of instant coffee or the like
US4365061A (en) 1980-10-17 1982-12-21 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. Inclusion complexes of cyclodextrins and strong inorganic oxy-acids and process for their preparation
US4438106A (en) 1981-07-16 1984-03-20 Kureha Kagaku Kabushiki Kaisha Inclusion compound of eicosapentaenoic acid or docosahexaenoic acid with cyclodextrin
US4547365A (en) 1982-11-08 1985-10-15 Shiseido Company Ltd. Waving lotion for cold waving
US4529608A (en) 1982-11-08 1985-07-16 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt Honey powder preserving its natural aroma components
US4751095A (en) 1983-07-28 1988-06-14 Karl Curtis L Aspartame stabilization with cyclodextrin
US4675395A (en) 1984-03-14 1987-06-23 Seiwa Technological Laboratories Limited Cyclodextrin inclusion compound and process for its preparation
US4596795A (en) 1984-04-25 1986-06-24 The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives
US4616008A (en) 1984-05-02 1986-10-07 Takeda Chemical Industries, Ltd. Antibacterial solid composition for oral administration
US4632832A (en) 1984-08-15 1986-12-30 Morinaga Milk Industry Co., Ltd. Instant creaming powder
US4636343A (en) 1984-09-10 1987-01-13 Ichiro Shibanai Process for the preparation of insect repelling/killing film
US4728510A (en) 1985-06-13 1988-03-01 Japan Liquid Crystal Co., Ltd. Bath preparations and method for producing the same
US4732759A (en) 1985-06-13 1988-03-22 Japan Liquid Crystal Co., Ltd. Bath preparations and method for producing the same
US4663316A (en) 1985-06-28 1987-05-05 Warner-Lambert Company Antibiotic clathrates and pharmaceutical compositions thereof
US5571782A (en) 1990-03-06 1996-11-05 The Procter & Gamble Company Solid consumer product compositions containing small particle cyclodextrin complexes
US5635238A (en) 1990-03-06 1997-06-03 The Procter & Gamble Company Solid consumer product compositions containing small particle cyclodextrin complexes

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Chen, Abstracts of Papers of the American Chemical Society, v. 206 (1-2), p. AGFD 135 (1993).
J. Szejtli, "Industrial Applications of Cyclodextrins", Inclusion Compounds, v. 3, p. 331-390 (1984).
József Szejtli, "Cyclodextrin Technology", Topics in Inclusion Science, P. 307-334.
K. Lindner, "Using Cyclodextrin Aroma Complexes in the Catering", Die Nahrung, v. 26 (7-8), p. 675-680 (1982).
L. Szente and J. Szejtli, "Molecular Encapsulation of Natural and Synthetic Coffee Flavor With beta-Cyclodextrin", Journal of Food Science, v. 51(4), p. 1024-27 (1986).
L. Szente and J. Szejtli, "Molecular Encapsulation of Natural and Synthetic Coffee Flavor With β-Cyclodextrin", Journal of Food Science, v. 51(4), p. 1024-27 (1986).

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* Cited by examiner, † Cited by third party
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US20040057910A1 (en) * 2002-09-24 2004-03-25 The Procter & Gamblecompany Oral products having an aesthetic layer
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US20040180125A1 (en) * 2003-03-11 2004-09-16 Plank David W. Cyclodextrin-containing compositions and methods
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US20060088648A1 (en) * 2004-10-15 2006-04-27 Teoh Heidi M Microwave popcorn with thaumatin and method of preparation
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US20060134132A1 (en) * 2004-12-20 2006-06-22 Watkins Jackie M Protective barriers for micronutrients, phytochemicals, and nutraceuticals
US20090029020A1 (en) * 2005-06-13 2009-01-29 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
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US20100119680A1 (en) * 2007-05-23 2010-05-13 Alan Parker Flavouring composition
US20090022856A1 (en) * 2007-07-16 2009-01-22 Philip Morris Usa Inc. Oral pouch products with immobilized flavorant particles
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